[10] After earning a degree in Business Administration from the University of Kentucky,[11] McPeek interviewed for a position as a stockbroker in New York, but decided his career to be in the Thoroughbred racing industry by taking a job as a hot walker for Shug McGaughey.

McPeek saddled his first winner, Final Destroyer, owned by his father, at River Downs (now known as Belterra Park) in October 1985.

[14] Later that year, with the Triple Crown on the line for War Emblem, McPeek's colt Sarava caused an upset by winning the Belmont Stakes at odds of 70:1.

[12] By June 2005 McPeek decided to scale back his training operations, feeling that his stable of 160 horses, in six states, had become too large.

He chose to focus on being a bloodstock agent, a shift that led to his purchase of the future two-time Horse of the Year, Curlin, at the Keeneland Yearling September Sale for $57,000.

McPeek's approach to purchasing horses is a system he developed early in his career when working with limited budgets.

[2] One of McPeek's early successes came in 1993 with Tejano Run, a horse he purchased for $6,000 who went on to finish second in the Kentucky Derby[2] and earn $1.1 million in purses throughout his career.

Despite her modest pedigree, she won over $2.4 million during her career and became a Blue Hen mare, producing champions like Take Charge Brandi and Omaha Beach.

This shift led to one of his most famous purchases, Curlin, acquired for a modest sum of $57,000 due to an inflamed ankle.

Jenna graduated with a Bachelor of Science in Biochemistry and Molecular Biology and also majored in Equine Pre-veterinary studies.